Get the 250 and enjoy the fresh air. The yahoos with the beer coolers are fewer and farther between than you think. From my experience, if you're in an area where they have to trailer their ATV/SXS to the trail head they're pretty much nonexistent.That's pee on my cornflakes.
Some of the other posts had me thinking about a light, maybe 250cc blue plate and low speed gravel or dirt road excursions. Getting to the roads without the encumbrances of trailers would have to be worked out.
My uncle was a mechanic in WWII and when the roads were rough he said the dispatch riders preferred the light bikes because if they had to hit the ditch to avoid the enemy they could pull the bike out on their own. Once the areas were secure they liked the Harleys and Indians. I have no desire to pull a Goldwing out of a ditch.
I was envisioning a bucolic ride and the smell of the forest. Now it's beer buggys and mayhem.
As Mike said, you can plonk around for hours east of the city and have a great day of exploring.